3-O-dibenzylphosphate-2,4,6-tri-O-benzyl-D-myo-inositol | 797038-13-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-dibenzylphosphate-2,4,6-tri-O-benzyl-D-myo-inositol
• CAS: 797038-13-2
• 化学式: C₄₁H₄₃O₉P
• 分子量: 710.761
• InChiKey: NNLLOBCBRRJKRO-MPJXNKHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  51.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  112.91
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-O-dibenzylphosphate-2,4,6-tri-O-benzyl-D-myo-inositol 在 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成 Phosphoric acid benzyl ester (1S,2S,3R,4S,5S,6S)-2,4,6-tris-benzyloxy-3,5-dihydroxy-cyclohexyl ester
  参考文献：
  名称：

  简化的磷脂酰肌醇（PI），PI3P，PI3,5P 2和脱氧类似物的合成作为潜在的生物探针

  摘要：

  据报道，磷脂酰肌醇（PI），磷脂酰肌醇-3-磷酸酯（PI3P），磷脂酰肌醇-3,5-双磷酸酯（PI3,5P 2）和一系列脱氧形式的高度直接的全合成。进行每个合成以递送光学纯形式的靶标。对于每个合成中的关键步骤是催化不对称磷酸化反应，影响适当的desymmetrization肌醇-肌醇的前体。然后采用通用前体的面向多样性的策略对每种目标化合物进行精细加工。除三种天然产物外，还报道了几种其他简化的脱氧PI类似物的总合成方法。这些合成为这些膜相关信号分子的极性头基/生物靶标相互作用的高精度生物学研究奠定了基础。

  DOI：

  10.1021/jo060702s
• 作为产物：
  描述：

  1,5-O-bis(t-butyldimethylsilyl)-3-O-dibenzylphosphate-2,4,6-tri-O-benzyl-D-myo-inositol 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 3-O-dibenzylphosphate-2,4,6-tri-O-benzyl-D-myo-inositol
  参考文献：
  名称：

  Asymmetric Syntheses of Phosphatidylinositol-3-Phosphates with Saturated and Unsaturated Side Chains through Catalytic Asymmetric Phosphorylation

  摘要：

  Highly direct asymmetric syntheses of phosphatidylinositol-3-phosphate (PI3P) in each enantiomerically pure form have been achieved. The key step involves catalytic asymmetric phosphorylation of meso-myo-inositol derivatives through desymmetrization. Protecting group schemes have been employed that allow for synthesis of PI3P with either saturated or arachidonate side chains, in analogy to the naturally occurring systems. Syntheses in each enantiomeric series are reported that rely on the choice of enantioselective peptide-based catalyst to define the enantiomeric series in which the syntheses are carried out.

  DOI：

  10.1021/ja0466098

文献信息

• Catalyst-dependent syntheses of phosphatidylinositol-5-phosphate–DiC8 and its enantiomer
  作者：Katherine J. Kayser-Bricker、Peter A. Jordan、Scott J. Miller

  DOI：10.1016/j.tet.2008.03.037

  日期：2008.7

  Peptide-based catalysts have been applied to the enantioselective syntheses of the title Compounds, with this being the first report of the synthesis of an ent-PI5P analogue. The key steps in the synthesis involve asymmetric phosphorylation catalysis. Additional maneuvers were developed with a protecting groups scheme that enabled efficient, streamlined syntheses of these important mediators of biochemical events. (C) 2008 Elsevier Ltd. All rights reserved.
• A Fully Synthetic and Biochemically Validated Phosphatidyl Inositol-3-Phosphate Hapten via Asymmetric Synthesis and Native Chemical Ligation
  作者：Brent D. Chandler、Anne L. Burkhardt、Klaudia Foley、Courtney Cullis、Denise Driscoll、Natalie Roy D’Amore、Scott J. Miller

  DOI：10.1021/ja410750a

  日期：2014.1.8

  We report the synthesis and biochemical validation of a phosphatidyl inositol-3 phosphate (PI3P) immunogen. The inositol stereochemistry was secured through peptide-catalyzed asymmetric phosphorylation catalysis, and the subsequent incorporation of a cysteine residue was achieved by native chemical ligation (NCL). Conjugation of the PI3P hapten to maleimide-activated keyhole limpet hemocyanin (KLH) provided a PI3P immunogen, which was successfully used to generate selective PI3P antibodies. The incorporation of a sulfhydryl nucleophile into a phosphoinositide hapten demonstrates a general strategy to reliably access phosphoinositide immunogens.
• US4906761A
  申请人：——

  公开号：US4906761A

  公开（公告）日：1990-03-06
• US5055597A
  申请人：——

  公开号：US5055597A

  公开（公告）日：1991-10-08